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Booking Annoyance

I tried to book the following itinerary itinerary: SFO-OAX OAX-MEX bus to Cuernavaca
MEX-SFO

First of all, we were generally given a two layover flight to OAX with this combination. Then we could not find anything but an early morning flight or a late afternoon flight from OAX to MEX. Finally, we had only an early morning flight or evening flight from MEX to SFO. It became too complicated, so we decided to do just one week in Oaxaca, and lo and behold, there is a mid-day flight from OAX to MEX, and the MEX to SFO flight leaves at 3 p.m., a time for which we never had an option on the original itinerary, and for $100 less. The one possible problem is that we have only 30 minutes to transfer in Mexico City, but since it is on our return flight I figure that we can put up with the potential hassle of missing a flight.

I was using Kayak, and then tried Aero Mexico (which is the airline for our RT tickets), and the results were the same. It appears that while the 3 p.m. flight from MEX to SFO is part of a relatively inexpensive RT package, it becomes a deal breaker when doing an open jaw which basically only adds a couple of non-flying days between the return legs from OAX to SFO.

I recently had to book TPA through Oaxaca and couldn't find a way to avoid two stops, Houston and MEX. The trouble I ran into was an inability to control the layover in MEX on the way back: I wanted to spend the afternoon and night in MEX and proceed to Houston and Tampa in the morning, but every site I tried wanted me to overnight in Houston. So I paid a travel agent in my city $20 (total) to book it for me the way I wanted it.